Wow, is the clothing in that picture inaccurate. However, it is somewhat interesting in that it is one of the earliest pirate-fantasy images I've seen showing a pirate in riding boots. It comes from the 1846 four-volume set of French books 'Histoire des pirates et corsaires de l'Océan et de la Méditerranée depuis leur origine jusqu'à nos jours' by P. Christian with engravings by A. Catel. In it you can find Henry Morgan in riding boots and Mary Read and some unnamed sailor in what almost look like brown booties!

Perhaps the mid-18th century French gave us the Pirate-riding boot connection? (That makes sense.) I wonder why the pirate-bootie connection never caught on?

https://previews.magnoliabox.com/.../MUS-FAPC1114_850.jpg

Here's another male pirate in more distinct booties from the same work. (A 'brother of the coast'.)

Perhaps Pyle and Wyeth copied the riding boots from Catel, but didn't find the bootie look as manly?

https://previews.magnoliabox.com/.../MUS-FAPC1114_850.jpg